Piperidine-1-carboximidamide Hydrochloride → HCID 67517523, compound

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Reaction Steps

A mixture of 3-(dimethylamino)-1-(2-methyl-3-f uranyl)-2-(2-methyl-4-pyridinyl)-2-propen-1-one (270 mg, 1 mmol) and 1-piperidinecarboximidamide hydrochloride (245 mg, 1.500 mmol) in ethanol (4 ml) was stirred at room temperature. Potassium tert-butoxide (224 mg, 2.000 mmol) was added and the mixture was heated at reflux for 90 minutes. After cooling to room temperature the solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 30-100% ethyl acetate in isohexane. The resulting oil was dissolved in dichloromethane (2 ml) and was treated with hydrogen chloride (1M in diethyl ether, 1 ml). The solvent was evaporated and the residue co-evaporated with diethyl ether (×2). The residue was triturated with diethyl ether and the resulting solid was collected, washed with diethyl ether and dried to give the title compound as a pale yellow solid (114 mg, 31%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.60 (2H, d), 8.55 (1H, s), 7.83 (1H, b), 7.58-7.54 (1H, m), 7.51 (1H, d), 6.03 (1H, d), 3.90-3.85 (4H, m), 2.67 (3H, s), 2.38 (3H, s), 1.70-1.53 (6H, m).

Provenance & Evidence